ExplorEnz: EC 1.14.20.4

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1.14.20.4

Accepted name:

anthocyanidin synthase

Reaction:

a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O₂ = an anthocyanidin + succinate + CO₂ + 2 H₂O (overall reaction)
(1a) a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O₂ = a (4S)- 2,3-dehydroflavan-3,4-diol + succinate + CO₂ + H₂O
(1b) a (4S)- 2,3-dehydroflavan-3,4-diol = an anthocyanidin + H₂O

For diagram of anthocyanin biosynthesis, click here

Glossary:

taxifolin = 3,4-dihydroquercitin

Other name(s):

leucocyanidin oxygenase; leucocyanidin,2-oxoglutarate:oxygen oxidoreductase; ANS (gene name)

Systematic name:

(2R,3S,4S)-leucoanthocyanidin,2-oxoglutarate:oxygen oxidoreductase

Comments:

The enzyme requires iron(II) and ascorbate. It is involved in the pathway by which many flowering plants make anthocyanin flower pigments (glycosylated anthocyandins). The enzyme hydroxylates the C-3 carbon, followed by a trans diaxial elimination, forming a C-2,C-3 enol. The product loses a second water molecule to form anthocyanidins. When assayed in vitro, non-enzymic epimerization of the product can lead to formation of dihydroflavanols. Thus when the substrate is leucocyanidin, a mixture of (+)-taxifolin and (+)-epitaxifolin are formed. The enzyme can also oxidize the formed (+)-taxifolin to quercetin (cf. EC 1.14.20.6, flavonol synthase) [2,3].

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc, PDB, CAS registry number: 180984-01-4

References:

1.	Saito, K., Kobayashi, M., Gong, Z., Tanaka, Y. and Yamazaki, M. Direct evidence for anthocyanidin synthase as a 2-oxoglutarate-dependent oxygenase: molecular cloning and functional expression of cDNA from a red forma of Perilla frutescens. Plant J. 17 (1999) 181–190. [DOI] [PMID: 10074715]
2.	Turnbull, J.J., Sobey, W.J., Aplin, R.T., Hassan, A., Firmin, J.L., Schofield, C.J. and Prescott, A.G. Are anthocyanidins the immediate products of anthocyanidin synthase? Chem. Commun. (2000) 2473–2474.
3.	Wilmouth, R.C., Turnbull, J.J., Welford, R.W., Clifton, I.J., Prescott, A.G. and Schofield, C.J. Structure and mechanism of anthocyanidin synthase from Arabidopsis thaliana. Structure 10 (2002) 93–103. [DOI] [PMID: 11796114]
4.	Turnbull, J.J., Nagle, M.J., Seibel, J.F., Welford, R.W., Grant, G.H. and Schofield, C.J. The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity. Bioorg. Med. Chem. Lett. 13 (2003) 3853–3857. [DOI] [PMID: 14552794]
5.	Wellmann, F., Griesser, M., Schwab, W., Martens, S., Eisenreich, W., Matern, U. and Lukacin, R. Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin. FEBS Lett. 580 (2006) 1642–1648. [DOI] [PMID: 16494872]

[EC 1.14.20.4 created 2001 as EC 1.14.11.19, transferred 2018 to EC 1.14.20.4]